3-Methoxyamphetamine

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3-Methoxyamphetamine
3-Methoxyamphetamine.png
Clinical data
Routes of
administration		Oral
ATC code
  • none
Identifiers
IUPAC name
  • 1-(3-methoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
SMILES
  • NC(C)CC1=CC=CC(OC)=C1
InChI
  • InChI=1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3 checkY
  • Key:VEJWNIYARKAHFI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  

meta-Methoxyamphetamine[1] (MMA), also known as 3-methoxyamphetamine (3-MA), is a stimulant drug from the amphetamine family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA),[2] although with a slightly different ratio of monoamine release, being a combined serotonin, dopamine, and norepinephrine releasing agent rather than a fairly selective serotonin releaser like PMA.[3][4] 3-Methoxyamphetamine has similarly appeared on the illicit market as a designer drug alternative to MDMA, although far more rarely than its infamous positional isomer.[5] It produces gepefrine, a cardiac stimulant, as one of its major metabolites.[6]

See also[]

References[]

  1. ^ GB 1527479, "Acid Addition Salts of D-(+)-1-(3-Hydroxyphenyl)-2-Aminopropane and Their Manufacture and Use" 
  2. ^ Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior. 22 (5): 723–9. doi:10.1016/0091-3057(85)90520-9. PMID 3839309. S2CID 22341227.
  3. ^ Tseng LF, Menon MK, Loh HH (May 1976). "Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue". The Journal of Pharmacology and Experimental Therapeutics. 197 (2): 263–71. PMID 1271280.
  4. ^ Menon MK, Tseng LF, Loh HH (May 1976). "Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines". The Journal of Pharmacology and Experimental Therapeutics. 197 (2): 272–9. PMID 946817.
  5. ^ Dal Cason TA (June 2001). "A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone". Forensic Science International. 119 (2): 168–94. doi:10.1016/S0379-0738(00)00425-4. PMID 11376983.
  6. ^ Midha KK, Cooper JK, Bailey K, Hubbard JW (February 1981). "The metabolism of 3-methoxyamphetamine in dog, monkey and man". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 11 (2): 137–46. doi:10.3109/00498258109045284. PMID 6894510.
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